(R)-N-[3-nitro-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide → (R)-N-[3-Amino-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Participants

Reaction Steps

To a stirred solution of (R)-N-[3-nitro-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 3) (14.3 g) in EtOAc (250 ml) under a hydrogen atmosphere was added 10% palladium on carbon (1.6 g). The reaction mixture was allowed to stir at room temperature overnight; the mixture was filtered through a pad of diatomaceous earth and volatile material was removed by evaporation to give the title compound (13 g) as a brown solid. NMR (CDCl3) 1.75 (s, 3H), 4.00 (s, 1H), 4.10 (brs, 2H), 6.61 (d, 1H), 7.08 (t, 1H), 7.72 (d, 1H), 8.77 (brs, 1H); m/z: 281.

Provenance & Evidence